Sodium Carbonate → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1698073노트

반응식

HRID 1698073 반응식
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 529878072-Bromobenzo[d]thiazol-6-amine

생성물 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine수율 96.3%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
140 °C

실험 절차

A mixture of 2-bromo-1,3-benzothiazol-6-amine (53 mg, 0.23 mmol), 2-methoxy-5-pyridineboronic acid (50 mg, 0.327 mmol), Pd(dppf)Cl2*DCM (8 mg, 0.01 mmol) and sodium carbonate (0.1 g, 1 mmol) in THF/water (9:1, 3 mL) was heated at 140° C. for 10 minutes in a microwave reactor under argon atmosphere. The mixture was filtered and washed with THF/water (9:1). After having added DCM to the filtrate, the organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane), to yield the title compound (57 mg) as an off-white solid. 1H NMR (CHLOROFORM-d) δ 8.68 (d, 1H) 8.16 (dd, 1H) 7.74 (d, 1H) 7.06 (d, 1H) 6.70-6.81 (m, 2H) 3.94 (s, 3H) 3.77 (s, 2H); MS m/z (M+H) 258.

후처리

  1. filtrationThe mixture was filtered
  2. washwashed with THF/water (9:1)
  3. additionAfter having added DCM to the filtrate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-659e8d2bd817477f9fb1ccc4913eba1b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163928B2

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